Biomimetic cyclization of cnicin to malacitanolide, a cytotoxic eudesmanolide from Centaurea malacitana

被引：29

作者：

Barrero, AF ^{[1
]}

Oltra, JE ^{[1
]}

Morales, V ^{[1
]}

Alvarez, M ^{[1
]}

RodriguezGarcia, I ^{[1
]}

机构：

[1] UNIV ALMERIA,FAC CIENCIAS EXPT,DEPT QUIM ORGAN,ALMERIA 04120,SPAIN

来源：

JOURNAL OF NATURAL PRODUCTS | 1997年 / 60卷 / 10期

关键词：

D O I：

10.1021/np970040p

中图分类号：

Q94 [植物学];

学科分类号：

071001 [植物学];

摘要：

Malacitanolide (2), a new eudesmanolide isolated from the aerial parts of Centaurea malacitana, was characterized spectroscopically. The synthesis of 2 from cnicin (1), via the epoxide 3, confirmed the structure and stereochemistry of malacitanolide, as well as its biogenetic relationship with 1. Cytotoxic activity values for 2 are significantly higher than for 1.

引用

页码：1034 / 1035

页数：2

共 13 条

[1]

ADEKENOV CM, 1993, SIBIRSKII KHIM ZH+, P76

[2]

Barrero A. F., 1995, Fitoterapia, V66, P227

[3]

SYNTHESIS OF (+)-VERNOLEPIN RELATED-COMPOUNDS FROM GERMACRANOLIDES [J].

BARRERO, AF ;

OLTRA, JE ;

BARRAGAN, A .

TETRAHEDRON LETTERS, 1995, 36 (02) :311-314

[4]

BERENGERON RI, 1984, BIOCHEM BIOPH RES CO, V121, P848

[5]

SESQUITERPENE LACTONES AND FLAVONES FROM CENTAUREA-CINERARIA SUBSP UMBROSA [J].

BRUNO, M ;

HERZ, W .

PHYTOCHEMISTRY, 1988, 27 (06) :1873-1875

[6]

SYNTHESIS AND BIOLOGICAL-ACTIVITY OF ALPHA-METHYLENE-GAMMA-BUTYROLACTONES [J].

HOFFMANN, HMR ;

RABE, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (02) :94-110

[7]

MARCO JA, 1992, PHYTOCHEM LIFE SCI A, V11, P159

[8]

FLAVONES, SESQUITERPENE LACTONES AND GLYCOSIDES ISOLATED FROM CENTAUREA-ASPERA VAR STENOPHYLLA [J].

PICHER, MT ;

SEOANE, E ;

TORTAJADA, A .

PHYTOCHEMISTRY, 1984, 23 (09) :1995-1998

[9]

RODRIGUES AAS, 1978, PHYTOCHEMISTRY, V17, P953

[10]

SESQUITERPENE LACTONES AND EUDESMANE DERIVATIVES FROM ONOPORDON-CARMANICUM [J].

RUSTAIYAN, A ;

AHMADI, B ;

JAKUPOVIC, J ;

BOHLMANN, F .

PHYTOCHEMISTRY, 1986, 25 (07) :1659-1662

← 1 2 →